IMPPAT Phytochemical information: 
Unii-72U0C7paav
Unii-72U0C7paav
Summary

SMILES: COc1ccc2c3c1Oc1c(O)c(OC)ccc1C1=C3N(CC2)[C@@]2(C1=O)C[C@H]1[C@]34[C@@H]2Oc2c4c(C[C@@H]1N(CC3)C)ccc2OC
InChI: InChI=1S/C36H34N2O7/c1-37-14-12-35-20-16-36(34(35)45-32-24(43-4)9-6-18(27(32)35)15-21(20)37)33(40)26-19-7-10-22(41-2)29(39)30(19)44-31-23(42-3)8-5-17-11-13-38(36)28(26)25(17)31/h5-10,20-21,34,39H,11-16H2,1-4H3/t20-,21+,34+,35-,36-/m1/s1
InChIKey: XWPPHGONALRWBY-IQXPYEGDSA-N
DeepSMILES: COcccccc6OccO)cOC))ccc6C=C%11NCC%15))[C@@]C5=O))C[C@H][C@@][C@@H]5Occ5cC[C@@H]9NCC%11))C))))ccc6OC
Scaffold Graph/Node/Bond level: O=C1C2=C3c4c(cccc4Oc4ccccc42)CCN3C12CC1C3Cc4cccc5c4C1(CCN3)C2O5
Scaffold Graph/Node level: OC1C2C3CCCCC3OC3CCCC4CCN(C2C43)C12CC1C3CC4CCCC5OC2C1(CCN3)C45
Scaffold Graph level: CC1C2C3CCCCC3CC3CCCC4CCC(C2C43)C12CC1C3CCCC14C1C(CCCC1CC24)C3
Functional groups: cOC; CN(C)C; cOc; cO; cC1=C(c)N(C)CC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzoxepines
ClassyFire Subclass: Dibenzoxepines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Morphinan alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
cancentrine
External chemical identifiers:
CID:CID_101588305; ZINC:ZINC000085881344; FDASRS:72U0C7PAAV
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Unii-72U0C7paav
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 606.68
Log P RDKit 4.55
Topological polar surface area (Å2) RDKit 89.93
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Unii-72U0C7paav
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.46
Unii-72U0C7paav
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes